Find Romantic Hotels in Kissimmee, FL from CA $119

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Find properties with these dates

Tonight
May 13 - May 14
Tomorrow
May 14 - May 15
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Top Kissimmee Romantic Hotels

Exterior
1-101 Legacy Dunes, Just steps from our beach style pool, minutes from Disney!
10.0 out of 10, Exceptional, (24)
"Great property everything. Was close by. The house was clean and had everything we needed :) thank you to the host! Highly recommend"
1-101 Legacy Dunes, Just steps from our beach style pool, minutes from Disney!
Exterior
1-304 Legacy Dunes, pool view from our balcony, just 4 miles from Disney
9.4 out of 10, Exceptional, (22)
"Fantastic"
1-304 Legacy Dunes, pool view from our balcony, just 4 miles from Disney
Exterior
14-206 Legacy Dunes Resort, 4 miles from Disney, relax and recharge, heated pool
9.2 out of 10, Wonderful, (29)
"This is a very nice two bed condo. It is nicely decorated and spotlessly clean. The owners got all the basics right; plenty of towels, basic starter provisions like toilet rolls, kitchen roll, washing liquid, dishwashers tablets, etc all provided. There is a nice view of the lake from the balcony. It was our second visit to Legacy Dunes and having stayed in several different places over the years, it is probably our favourite. Its a quiet gated complex with a nice pool. It’s located on the Irwin...
14-206 Legacy Dunes Resort, 4 miles from Disney, relax and recharge, heated pool
Exterior
1-103 Minutes from Disney with a heated beach style swimming pool, free cabanas
9.0 out of 10, Wonderful, (2)
"Location relative to the Pool is excellent. Cleanliness of the Condo was good. It had a skunk smell when we arrived. We cleared it quickly. The grounds and pool area was not cleaned daily. There were crews working on cleaning so maybe we were there at a bad time. This complex has many owners using their properties. The owners were very friendly with the renting guests. We will return to Legacy again"
1-103 Minutes from Disney with a heated beach style swimming pool, free cabanas
4 outdoor pools, cabanas (surcharge), pool umbrellas
Hilton Vacation Club Mystic Dunes Orlando
3.5 star property
8.8 out of 10, Excellent, (3102)
"We arrived in Orlando at 11am. We took a chance and called to see if a room was ready. We were told our room was ready and we could come on over and check in. Check in was quick and easy. Our 2 bedroom suite was clean and nice. We loved the full kitchen. We went and bought groceries instead of eating out every day. The balcony is huge and screened in. The property is beautiful and always clean. The pools have plenty of chairs and umbrellas. We liked the text message communication with the front...
The price is CA $119
CA $182 total
includes taxes & fees
May 19 - May 20
Hilton Vacation Club Mystic Dunes Orlando
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1118)
"Great hotel "
Reunion Resort & Golf Club
Exterior
1-105 Legacy Dunes, tropical, beach style walk-in swimming pool, gated, security
8.6 out of 10, Excellent, (13)
"Great price, location and process"
1-105 Legacy Dunes, tropical, beach style walk-in swimming pool, gated, security
2 outdoor pools, pool umbrellas, sun loungers
Star Island Resort and Club
3.5 star property
7.8 out of 10, Good, (1166)
"Relaxing place"
The price is CA $137
CA $179 total
includes taxes & fees
May 14 - May 15
Star Island Resort and Club
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

Searching for romantic hotels in Kissimmee?
Are you and your partner in need of a romantic escape? Couples choose Kissimmee for its top-notch restaurants and renowned opera house. If you’re a pair that loves cultural attractions, you might check out Osceola Performing Arts Center, Medieval Times, or Capone’s Dinner Show. Whether you want to get a couple’s massage or enjoy a candlelit dinner, you can pick from 44 hotels and other accommodations in Kissimmee to make for the perfect weekend away.
What's the best place to stay for couples in Kissimmee?
All Suite Resort near Old Town Amusement Park and Disney World is a favorite resort for couples, and features private pools and kitchens. Another choice for your romantic getaway is Magical Newly Renovated 10 minutes to Disney 2Bed,2Bath.
How many romantic hotels can we expect to find in Kissimmee?
Expedia has 44 romantic Kissimmee hotels for you to get cozy in.
When is the best time to visit Kissimmee?
If you’re hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Kissimmee: The hottest months are usually July and August with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Kissimmee are August, July, September, and June, with each month seeing an average of 8 inches of rainfall.
What is there to do in Kissimmee?
There’s nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all that Kissimmee has to offer. If you’re hoping to experience some of the local culture, you’ll love Kissimmee for its lively festivals, fun-filled attractions, and major shopping area. You might think about stopping by Disney’s Animal Kingdom® Theme Park, Walt Disney World® Resort, or Old Town while you’re seeing the sights.
What's the best way to get to Kissimmee and around town during my romantic getaway?
This information about transportation options in Kissimmee might help your romantic getaway go off without a hitch: Make your way to Kissimmee with a flight to Kissimmee, FL (ISM-Kissimmee Gateway), which is the closest major airport located 1.8 mi (2.9 km) from the city center. Nearby metro stations include Tupperware Station and Poinciana Station. To see more of the larger area, hop aboard a train at Kissimmee Station.